AU2014271925B2

AU2014271925B2 - Control agents for honeybee parasites and control method for honeybee parasites using same

Info

Publication number: AU2014271925B2
Application number: AU2014271925A
Authority: AU
Inventors: Ryo Horikoshi; Masaaki Mitomi
Original assignee: Meiji Seika Pharma Co Ltd
Current assignee: Meiji Seika Pharma Co Ltd
Priority date: 2013-05-27
Filing date: 2014-05-27
Publication date: 2017-11-23
Anticipated expiration: 2034-05-27
Also published as: EA029532B1; JP5704737B1; PL2907390T3; EA201591903A1; JPWO2014192717A1; CN105283074B; WO2014192717A1; EP2907390A1; KR20160013925A; CN105283074A; HUE032876T2; AU2014271925A1; US9066517B2; US20150057288A1; BR112015027002A2; CA2910879A1; TW201536744A; EP2907390A4; EP2907390B1; MX2015014067A

Abstract

This control method for honeybee parasites is highly safe for honeybees and exhibits an excellent controlling effect on honeybee parasites by using a honeybee parasite control agent which includes at least one from among the compounds represented by formula (I) and the acid addition salts thereof.

Description

[DESCRIPTION]

[Title of Invention] PEST CONTROL AGENTS FOR HONEYBEE PARASITIC PESTS, AND PEST CONTROL METHOD FOR HONEYBEE PARASITIC PESTS USING THE PEST CONTROL AGENTS

[Technical Field]

The present invention relates to pest control agents for controlling pests such as honeybee parasitic pests, and a pest control method using the pest control agents.

[Background Art]

Not only are honeybees used for collecting honey, but also the use ratio as beneficial pollinator insects is now increasing. It has been reported that the annual economic value of honeybee pollination has reached 5 to 10 billion dollars in the United States and is expected to be 100 or more times the economic value of honeybee products including honey. The number of colonies of bees kept at present is 9 million in China, 9 million in the regions of the former Soviet Union, 3 million in the United States, 3 million in Mexico, 2 million in Brazil, 1.50 million in Argentina, and 0.20 million in Japan. Thus, the beekeeping industry is one of important sectors of agriculture in any countries in the world.

Recently, Colony Collapse Disorder (CCD) has become problem worldwide, and serious influences on the beekeeping industry due to the decrease in the number of honeybee colonies have been reported. It is said that Colony Collapse Disorder is attributable to adverse influences on honeybees from honeybee parasitic pests including Varroa destructor (Kagaku to Seibutsu (Bioscience & Biotechnology), 2010, vol. 48, no. 8, pp. 577 to 582 (NPL 1)), neonicotinoid-based chemicals, or the like.

At present, amitraz, fluvalinate, coumaphos, formic acid, sucrose octanoate ester, organic acids such as β-acid, and the like are known as chemicals for Varroa destructor control. In addition, chemicals under studies include a triazine-based insecticide cyromazine (International Publication No. W02012/156342 (PTL 1)), a hydrazine-based insecticide bifenazate (International Publication No. W02012/156344 (PTL 2)), and the like. However, the number of chemicals highly safe to honeybees is still small, and there are problems of parasitic pests resistant to insecticides. Hence, a chemical for honeybee parasitic pest control having a novel action and high safety is strongly desired.

In such circumstances, a novel chemical for honeybee parasitic pest control has been further searched for. A compound of the present invention includes a compound described as a pest control agent in Japanese Patent No. 4993641 (PTL 3) and

International Publication No. W02013/129692 (PTL 4) . However, the literatures do not state at all that the pest control agent has an effect against honeybee parasitic pests. Moreover, European Patent Application Laid-Open No. 432600 (PTL 5) discloses a compound having a structure similar to the compound of the present invention, but fails to provide any description or suggestion regarding safety to honeybees and effect against honeybee parasitic pests .

Further, Japanese Unexamined Patent Application Publication No. Hei 5-78323 (PTL 6) and European Patent Application Laid-Open No. 268915 (PTL 7) disclose a structural formula of N— [1— ( (6 — chloropyridin-3-yl)methyl)pyridine-2(1H)-ylidene]-2,2,2-1rifluoroacetamide , but fail to provide any description or suggestion regarding safety to honeybees and effect against honeybee parasitic pests .

Chemische Berichte (1955), 88, 1103-8 (NPL 2) discloses a plurality of compounds having a ring structure similar to the compound of the present invention, but the compounds are disclosed only as synthetic intermediates.

European Patent Application Laid-

Open No. 259738 (PTL 8) discloses a plurality of com pounds having a ring structure similar to the compou nd of the present invention, but fails to disclose o r suggest a compound having a trifluoroacetic acid i mino structure.

[Citation List] [Patent Literature] [PTL 1] International Publication No. WO2012/15634 2 [PTL 2 ] International Publication No. WO2012/156344 [PTL 3] Japanese Patent No. 4993641 [PTL 4 ] International Publication No. WO2013/129692 [PTL 5 ] European Patent Application Laid-

Open No . 4 32 600 [PTL 6 ] Japanese Unexamined Patent Application Publication No. Hei 5-78323 [PTL 7 ] European Patent Application Laid-

Open No. 268915 [PTL 8 ] European Patent Application Laid-

Open No. 259738 [Non Patent Literature] [NPL 1] Kagaku to Seibutsu (Bioscience &

Biotechnology), 2010, vol. 48, no. 8, pp. 577 to 582 [NPL 2] Chemische Berichte (1955), 88, 1103-8 [Summary of Invention]

The present invention advantageously provides an excellent pest control method for honeybee parasitic pests by using a chemical having high safety to honeybees and novel actions.

The present inventors have intensively studied, and as a result, have found that a compound represented by the following Formula (I) may show excellent pest control effects against honeybee parasitic pests. The present invention is based on the finding.

Therefore, the present invention provides a honeybee parasitic pest control agent containing at least one of a compound represented by the following Formula (I) and acid addition salts thereof, as well as a method for controlling honeybee parasitic pests by using the pest control agent.

Specifically, the present invention provides the following aspects. (1) A honeybee parasitic pest control agent, comprising: at least one of a compound represented by the following Formula (I) or acid addition salts thereof as an active ingredient.

[Chemical Formula 1]

[in the formula (I), Ar represents a phenyl group which may be substituted, a 5- to 6-membered heterocycle which may be substituted, or a 4- to 10-membered heterocycloalkyl group, A represents a 5- to 10-membered heterocycle having a unsaturated bond including one or more nitrogen atoms, and has an imino group substituted with an R group at a position adjacent to the nitrogen atom present on the cycle, Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a Cl to C6 alkyl group which may be substituted with a halogen atom, a Cl to C6 alkyloxy group which may be substituted with a halogen atom, a cyano group, or a nitro group, and R represents any one of groups represented by the following Formulae (a) to (e), (y) or (z), [Chemical Formula 2]

here, Ri represents a hydrogen atom, a substituted Cl to C6 alkyl group, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, or a pentafluorophenyl group, R.2 represents a Cl to C6 alkyl group which may be substituted with a halogen atom, an unsubstituted C3 to C6 branched or cyclic alkyl group, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to CIO) aryl group, a substituted or unsubstituted 5- to 10-membered heterocycle, or a substituted or unsubstituted benzyl group, R3 represents a Cl to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to CIO) aryl group, a substituted or unsubstituted (C6 to CIO) aryl (Cl to C6) alkyl group, a substituted or unsubstituted (C6 to CIO) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to CIO) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (Cl to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (Cl to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5-to 10-membered heterocycle (C2 to C6) alkynyl group, a (Cl to C4) alkoxy (Cl to C5) alkyl group, a (Cl to C4) alkoxy (C2 to C5) alkenyl group, a (Cl to C4) alkoxy (C2 to C5) alkynyl group, a (Cl to C4) alkylthio (Cl to C5) alkyl group, a (Cl to C4) alkylthio (C2 to C5) alkenyl group, or a (Cl to C4) alkylthio (C2 to C5) alkynyl group, R4 represents a hydrogen atom, a formyl group, a Cl to C18 alkyl group which may be substituted, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to CIO) aryl group, a substituted or unsubstituted (C6 to CIO) aryl (Cl to C6) alkyl group, a substituted or unsubstituted (C6 to CIO) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to CIO) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (Cl to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10- membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (Cl to C6) alkyl group, a substituted or unsubstituted 5- to 1O-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5-to 10-membered heterocycle (C2 to C6) alkynyl group, a (Cl to C4) alkoxy (Cl to C5) alkyl group, a (Cl to C4) alkoxy (C2 to C5) alkenyl group, a (Cl to C4) alkoxy (C2 to C5) alkynyl group, a (Cl to C4) alkylthio (Cl to C5) alkyl group, a (Cl to C4) alkylthio (C2 to C5) alkenyl group, a (Cl to C4) alkylthio (C2 to C5) alkynyl group, or a group represented by the following Formulae (f) to (n) [Chemical Formula 3]

[here, R4a, R4b and R4c represent a Cl to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to CIO) aryl group, a substituted or unsubstituted (C6 to CIO) aryl (Cl to C6) alkyl group, a substituted or unsubstituted (C6 to CIO) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to CIO) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (Cl to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-member ed heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (Cl to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5-to 10-membered heterocycle (C2 to C6) alkynyl group, a (Cl to C4) alkoxy (Cl to C5) alkyl group, a (Cl to C4) alkoxy (C2 to C5) alkenyl group, a (Cl to C4) alkoxy (C2 to C5) alkynyl group, a (Cl to C4) alkylthio (Cl to C5) alkyl group, a (Cl to C4) alkylthio (C2 to C5) alkenyl group, or a (Cl to C4) alkylthio (C2 to C5) alkynyl group, R4d represents a Cl to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to CIO) aryl group, or a substituted or unsubstituted 5- to 10-membered heterocycle, and R4e and R4f each independently represent a hydrogen atom, a Cl to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to CIO) aryl group, or a substituted or unsubstituted 5- to 10-membered heterocycle], R5 represents a Cl to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to CIO) aryl group, a substituted or unsubstituted (C6 to CIO) aryl (Cl to C6) alkyl group, a substituted or unsubstituted (C6 to CIO) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to CIO) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (Cl to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (Cl to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5-to 10-membered heterocycle (C2 to C6) alkynyl group, a (Cl to C4) alkoxy (Cl to C5) alkyl group, a (Cl to C4) alkoxy (C2 to C5) alkenyl group, a (Cl to C4) alkoxy (C2 to C5) alkynyl group, a (Cl to C4) alkylthio (Cl to C5) alkyl group, a (Cl to C4) alkylthio (C2 to C5) alkenyl group, or a (Cl to C4) alkylthio (C2 to C5) alkynyl group, R6 represents a hydrogen atom, a formyl group, a 0,0'-C1 to C4 alkyl phosphoryl group, a Cl to C18 alkyl group which may be substituted, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to CIO) aryl group, a substituted or unsubstituted (C6 to CIO) aryl (Cl to C6) alkyl group, a substituted or unsubstituted (C6 to CIO) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to CIO) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (Cl to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (Cl to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5-to 10-membered heterocycle (C2 to C6) alkynyl group, a (Cl to C4) alkoxy (Cl to C5) alkyl group, a (Cl to C4) alkoxy (C2 to C5) alkenyl group, a (Cl to C4) alkoxy (C2 to C5) alkynyl group, a (Cl to C4) alkylthio (Cl to C5) alkyl group, a (Cl to C4) alkylthio (C2 to C5) alkenyl group, a (Cl to C4) alkylthio (C2 to C5) alkynyl group, or a group represented by the following Formulae (o) to (x) [Chemical Formula 4]

[here, R6a, F-6b and R6c represent a Cl to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to CIO) aryl group, a substituted or unsubstituted (C6 to CIO) aryl (Cl to C6) alkyl group, a substituted or unsubstituted (C6 to CIO) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to CIO) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (Cl to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (Cl to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5-to 10-membered heterocycle (C2 to C6) alkynyl group, a (Cl to C4) alkoxy (Cl to C5) alkyl group, a (Cl to C4) alkoxy (C2 to C5) alkenyl group, a (Cl to C4) alkoxy (C2 to C5) alkynyl group, a (Cl to C4) alkylthio (Cl to C5) alkyl group, a (Cl to C4) alkylthio (C2 to C5) alkenyl group, or a (Cl to C4) alkylthio (C2 to C5) alkynyl group, R6d represents a Cl to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to CIO) aryl group, or a substituted or unsubstituted 5- to 10-membered heterocycle, R6e and R6f each independently represent a hydrogen atom, a Cl to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a (Cl to C4) alkoxy (Cl to C5) alkyl group, a (Cl to C4) alkylthio (Cl to C5) alkyl group, a substituted or unsubstituted (C6 to CIO) aryl group, a substituted or unsubstituted (C6 to CIO) aryl (Cl to C6) alkyl group, or a substituted or unsubstituted 5- to 10-membered heterocycle, R6g and R6h each independently represent a hydrogen atom, a Cl to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to CIO) aryl group, or a substituted or unsubstituted 5- to 10-membered heterocycle, and

Rei, R6j and R6k each independently represent a hydrogen atom, a Cl to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, or a substituted or unsubstituted (C6 to CIO) aryl group], and R7 represents a Cl to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C 6 to CIO) aryl group, a substituted or unsubstituted (C6 to CIO) aryl (Cl to C6) alkyl group, a substituted or unsubstituted (C6 to CIO) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to CIO) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (Cl to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 1O-membered heterocycle (Cl to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (Cl to C4) alkoxy (Cl to C5) alkyl group, a (Cl to C4) alkoxy (C2 to C5) alkenyl group, a (Cl to C4) alkoxy (C2 to C5) alkynyl group, a (Cl to C4) alkylthio (Cl to C5) alkyl group, a (Cl to C4) alkylthio (C 2 to C5) alkenyl group, or a (Cl to C4) alkylthio (C 2 to C5) alkynyl group,

Yi and Y2 represent an oxygen atom or a sulfur atom, and may be the same or different, and

Ry represents a Cl to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to CIO) aryl group, a substituted or unsubstituted (C6 to CIO) aryl (Cl to C6) alkyl group, a substituted or unsubstituted (C6 to CIO) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to CIO) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (Cl to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (Cl to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, or a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group,

Rz represents a Cl to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C 6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C 6 to CIO) aryl group, a substituted or unsubstituted (C6 to CIO) aryl (Cl to C6) alkyl group, a substituted or unsubstituted (C6 to CIO) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to CIO) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (Cl to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (Cl to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (Cl to C4) alkoxy (Cl to C5) alkyl group, a (Cl to C4) alkoxy (C2 to C5) alkenyl group, a (Cl to C4) alkoxy (C2 to C5) alkynyl group, a (Cl to C4) alkylthio (Cl to C5) alkyl group, a (Cl to C4) alkylthio (C2 to C5) alkenyl group, or a (Cl to C4) alkylthio (C2 to C5) alkynyl group, and n represents 1 or 2] (2) The honeybee parasitic pest control agent acoording to (1), comprising: at least one of an amine derivative represented by the following Formula (la) or acid addition salts thereof as the active ingredient.

[Chemical Formula 5]

(la) [here, Ar represents a pyridyl group which may be substituted with a halogen atom, a hydroxyl group, a Cl to C6 alkyl group which may be substituted with a halogen atom, a Cl to C6 alkyloxy group which may be substituted with a halogen atom, a cyano group, or a nitro group, or a pyrimidyl group which may be substituted with a halogen atom, a Cl to C4 alkyl group which may be substituted with a halogen atom, an alkyloxy group which may be substituted with a halogen atom, a hydroxyl group, a cyano group, or a nitro group, Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a Cl to C6 alkyl group which may be substituted with a halogen atom, a Cl to C6 alkyloxy group which may be substituted with a halogen atom, a cyano group, or a nitro group, and

Ri represents a Cl to C6 alkyl group which is substituted with halogen] (3) The honeybee parasitic pest control agent according to (1), comprising: at least one of an amine derivative represented by the following Formula (Ic) or acid addition salts thereof as the active ingredient.

[Chemical Formula 6]

(Ic) [here, Ar represents a pyridyl group which may be substituted with a halogen atom, a hydroxyl group, a Cl to C6 alkyl group which may be substituted with a halogen atom, a Cl to C6 alkyloxy group which may be substituted with a halogen atom, a cyano group, or a nitro group, or a pyrimidyl group which may be substituted with a halogen atom, a Cl to C4 alkyl group which may be substituted with a halogen atom, an alkyloxy group which may be substituted with a halogen atom, a hydroxyl group, a cyano group, or a nitro group, Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a Cl to C6 alkyl group which may be substituted with a halogen atom, a Cl to C6 alkyloxy group which may be substituted with a halogen atom, a cyano group, or a nitro group, and R3 represents a Cl to C6 alkyl group which may be substituted with halogen] (4) The honeybee parasitic pest control agent according to (1), wherein ring A in Formula (I) represented by the following Formula: [Chemical Formula 7]

is a ring with Formula (A-l): [Chemical Formula 8]

(A-l) and Y is a hydrogen atom, a halogen atom and a cyano group. (5) The honeybee parasitic pest control agent according to (1) or (4), wherein R in Formula (I) is a group with Formula (c): [Chemical Formula 9]

(c) . (6) The honeybee parasitic pest control agent according to (1) or (4), wherein R in Formula (I) is a group with Formula (a): [Chemical Formula 10]

(a) . (7) The honeybee parasitic pest control agent according to (1) or (4), wherein R in Formula (I) is a group with Formula (d): [Chemical Formula 11] and R4 represents a Cl to C18 alkyl group which may be substituted, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to CIO) aryl group, a substituted or unsubstituted (C6 to CIO) aryl (Cl to C6) alkyl group, a substituted or unsubstituted (C 6 to CIO) aryl (C 2 to C6) alkenyl group, a substituted or unsubstituted (C6 to CIO) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (Cl to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (Cl to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5-to 10-membered heterocycle (C2 to C6) alkynyl group, a (Cl to C4) alkoxy (Cl to C5) alkyl group, a (Cl to C4) alkoxy (C2 to C5) alkenyl group, a (Cl to C4)

alkoxy (C2 to C5) alkynyl group, a (Cl to C4) alkylthio (Cl to C5) alkyl group, a (Cl to C4) alkylthio (C2 to C5) alkenyl group, a (Cl to C4) alkylthio (C2 to C5) alkynyl group, and R.5 is a Cl to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom. (8) The honeybee parasitic pest control agent according to any one of (1) to (7), wherein Ar is any one of a 6-chloro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridy1 group, a 6-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group, and a 2-chloro-5-pyrimidyl group. (9) A pest control method for honeybee parasitic pests, wherein the method uses the honeybee parasitic pest control agent according to any one of (1) to (8). (10) The pest control method for honeybee parasitic pests according to (9), wherein the honeybee parasitic pests are any one of Varroa destructor, honeybee Tropilaelaps, and Acarapis woodi. (11) The pest control method for honeybee parasitic pests according to any one of (9) and (10), comprising spraying the honeybee parasitic pest control agent diluted with water or without dilution to a hive of honeybees such that the active ingredient is applied in an effective amount. (12) The pest control method for honeybee parasitic pests according to any one of (9) and (10), comprising bringing honeybees into contact with a paper or tape material having been dipped into or coated with the honeybee parasitic pest control agent such that the active ingredient is applied in an effective amount. (13) The pest control method for honeybee parasitic pests according to any one of (9) and (10), comprising mixing the honeybee parasitic pest control agent with water or a feed such that the active ingredient is applied in the effective amount. (14) The pest control method for honeybee parasitic pests according to any one of (9) and (10), comprising subjecting a plant to any one of foliar treatment, seed treatment, nursery tray treatment, soil treatment, trunk injection, and trunk coating, using the honeybee parasitic pest control agent diluted with water or without dilution, such that the active ingredient is applied in the effective amount to thereby control the honeybee parasitic pests .

[Advantageous Effects of Invention]

The honeybee parasitic pest control agent of the present invention is highly safe to honeybees and demonstrates excellent pest control effects against honeybee parasitic pests. Note that, in the present invention, the term "pest control" includes killing of honeybee parasitic pests, prevention of parasitism of honeybee parasitic pests in honeybees, and removal of honeybee parasitic pests parasitizing honeybees .

[Description of Embodiments] A compound (iminopyridine derivative) represented by Formula (I) may be prepared by the following method when each type of substituent of R is indicated.

[Chemical Formula 12]

A compound represented by Formula (I—1) may be obtained by reacting a compound represented by the following Formula (II—1) with a compound represented by ArCH2X [the definition of Ar, A, Y and Ri has the same meaning as the definition described above, and X represents a halogen atom or OTs, OMs and the like] in the presence or absence of a base.

[Chemical Formula 13]

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride; a carbonate such as potassium carbonate or sodium carbonate; an alkali metal hydroxide such as potassium hydroxide, and sodium hydroxide; tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene; and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine; as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide; nitriles such as acetonitrile; sulfoxides such as dimethyl sulfoxide; ethers such as diethyl ether and tetrahydrofuran; esters such as ethyl acetate and butyl acetate; aromatic hydrocarbons such as benzene, xylene and toluene; alcohols such as methanol, ethanol, propanol and isopropyl alcohol; ketones such as acetone and methyl ethyl ketone; aliphatic hydrocarbons such as hexane, heptane and octane; and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene; either alone or in combination of two or more thereof, but N,N-dimethylformamide and the like are preferably used.

The reaction may be performed usually at 0°C to 200°C, and it is preferred that reagents are added at 20°C to 40°C and the reaction is performed at 60°C to 80°C.

The compound represented by Formula (II—1) may be obtained by reacting a compound represented by Ri-C(=0)X, Ri-C (=0) OC (=0) Ri, RiC (=0) OR' [X represents a halogen atom or OTs, OMs and the like, R' represents a Cl to C6 alkyl group, and the definition of Ri, A and Y has the same meaning as the definition described above] and the like with a compound represented by the following Formula (III) in the presence or absence of a base.

[Chemical Formula 14]

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride; a carbonate such as potassium carbonate or sodium carbonate; an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide; tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene; and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine; as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide; nitriles such as acetonitrile; sulfoxides such as dimethyl sulfoxide; ethers such as diethyl ether and tetrahydrofuran; esters such as ethyl acetate and butyl acetate; aromatic hydrocarbons such as benzene, xylene and toluene; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methyl ethyl ketone; aliphatic hydrocarbons such as hexane, heptane and octane; halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene; and water; either alone or in combination of two or more thereof, but toluene, N,N-dimethylformamide, acetonitrile, ethers, dichloromethane, chloroform and the like are preferably used.

The reaction may be performed usually at -80°C to 100°C, and is performed preferably in a range from 20°C to 50°C.

The compound represented by Formula (II—1) may be obtained by reacting the compound represented by Formula (III) with a carboxylic acid represented by Ri-COOH [the definition of Ri has the same meaning as the definition described above] using a dehydration condensation agent in the presence or absence of a base, or may be obtained by performing the reaction using phosphorus pentaoxide, sulfuric acid, polyphosphoric acid, thionyl chloride, phosphorus oxychloride and oxalyl dichloride in the absence of a base.

It is possible to use a carbodiimide-based compound such as dicyclohexylcarbodiimide and l-ethyl-3-(3-[dimethylaminopropyl])carbodiimide hydrochloride as the dehydration condensation agent.

When the reaction is performed in the presence of a base, it is possible to use, for example, a carbonate such as potassium carbonate or sodium carbonate; tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene; and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine; as the base.

The reaction is preferably performed by using a solvent, and it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide; nitriles such as acetonitrile; sulfoxides such as dimethyl sulfoxide; ethers such as diethyl ether and tetrahydrofuran; esters such as ethyl acetate and butyl acetate; aromatic hydrocarbons such as benzene, xylene and toluene; ketones such as acetone and methyl ethyl ketone; aliphatic hydrocarbons such as hexane, heptane and octane; and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene; either alone or in combination of two or more thereof, but dichloromethane, chloroform and the like are preferably used.

The compound represented by Formula (I — 1) may be obtained by reacting a compound represented by Ri-C(=0)X, Ri-C(=0)OC(=0)Ri, RiC(=0)OR' [X represents a halogen atom or OTs, OMs and the like, R' represents a Cl to C6 alkyl group, and the definition of Ar, A, Y and Ri has the same meaning as the definition described above] and the like with a compound represented by the following Formula (IV) in the presence or absence of a base.

[Chemical Formula 15]

The compound represented by Formula (I — 1) may be obtained by reacting the above-described compound represented by Formula (IV) with a carboxylic acid represented by Ri-COOH [the definition of Ri has the same meaning as the definition described above] using a dehydration condensation agent in the presence or absence of a base, or may be obtained by performing the reaction using phosphorus pentaoxide, sulfuric acid, polyphosphoric acid, thionyl chloride, phosphorus oxychloride and oxalyl dichloride in the absence of a base.

It is possible to use a carbodiimide-based compound such as dicyclohexylcarbodiimide and l-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride as the dehydration condensation agent.

The compound represented by Formula (IV) may be obtained by reacting the above-described compound represented by Formula (III) with a compound represented by ArCH2X [the definition of Ar and X has the same meaning as the definition described above] in the presence or absence of a base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide; nitriles such as acetonitrile; sulfoxides such as dimethyl sulfoxide; ethers such as diethyl ether and tetrahydrofuran; esters such as ethyl acetate and butyl acetate; aromatic hydrocarbons such as benzene, xylene and toluene; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methyl ethyl ketone; aliphatic hydrocarbons such as hexane, heptane and octane; halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene; and water; either alone or in combination of two or more thereof, but N,N-dimethylformamide, acetonitrile, ethers, dichloromethane, chloroform and the like are preferably used.

The reaction may be performed usually at -80°C to 100°C, and is performed preferably in a range from 20°C to 80°C.

When Formula (I—1) is synthesized via Formula (II—1) from the compound represented by Formula (III), or when Formula (I — 1) is synthesized via Formula (IV) from the compound represented by Formula (III), the reaction may be continuously performed without taking out Formula (11 — 1) or Formula (IV), or the reactions from Formula (III) to Formula (I — 1) may be simultaneously performed in the same vessel.

[Chemical Formula 16]

The compound represented by Formula (1-2) may be obtained by reacting a compound represented by the following Formula (I-2a) with a compound represented by ArCH2X [the definition of Ar, A, Y and R2 has the same meaning as the definition described above, and X represents a halogen atom or OTs, OMs and the like] in the presence or absence of a base.

[Chemical Formula 17]

The compound represented by Formula (I-2a) may be obtained by reacting the above-described compound represented by Formula (III) with a compound represented by R.20C(=0)X (the definition of R2 and X has the same meaning as the definition described above] or represented by the following Formula (I-2b) in the presence or absence of a base .

[Chemical Formula 18]

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide; nitriles such as acetonitrile; sulfoxides such as dimethyl sulfoxide; ethers such as diethyl ether, and tetrahydrofuran; esters such as ethyl acetate and butyl acetate; aromatic hydrocarbons such as benzene, xylene and toluene; alcohols such as methanol, ethanol, propanol and isopropyl alcohol; ketones such as acetone and methyl ethyl ketone; aliphatic hydrocarbons such as hexane, heptane and octane; and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene; either alone or in combination of two or more thereof, but acetonitrile, dichloromethane or the like is preferably used.

The reaction may be performed usually at 0°C to 200°C, and is performed preferably at 20°C to 80°C.

The compound represented by Formula (1-2) may be obtained by reacting the above-described compound represented by Formula (IV) with a compound represented by R.20C(=0)X [the definition of R2 and X has the same meaning as the definition described above] or represented by the above-described Formula (I-2b) in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride; a carbonate such as potassium carbonate or sodium carbonate; an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide; tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3. Ο]non-5-ene; and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine; as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide; nitriles such as acetonitrile; sulfoxides such as dimethyl sulfoxide; ethers such as diethyl ether and tetrahydrofuran; esters such as ethyl acetate and butyl acetate; aromatic hydrocarbons such as benzene, xylene and toluene; alcohols such as methanol, ethanol, propanol and isopropyl alcohol; ketones such as acetone and methyl ethyl ketone; aliphatic hydrocarbons such as hexane, heptane and octane; and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene; either alone or in combination of two or more thereof, but acetonitrile, dichloromethane or the like is preferably used.

[Chemical Formula 19]

The compound represented by Formula (1-3) may be synthesized by acting a sulfurizing reagent on a compound [the definition of Ar, A, Y and R3 has the same meaning as the definition described above] represented by the following Formula (II-3a), which may be synthesized in the same manner as described in Formula (I — 1) , in the presence or absence of a base.

[Chemical Formula 20]

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride; a carbonate such as potassium carbonate or sodium carbonate; an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide; tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene; and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine; as the base, but potassium carbonate, sodium carbonate or the like is preferably used.

As the sulfurizing reagent, phosphorus pentasulfide, Lawesson's reagent, hydrogen sulfide and the like may be used.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide; nitriles such as acetonitrile; sulfoxides such as dimethyl sulfoxide; ethers such as diethyl ether and tetrahydrofuran; esters such as ethyl acetate and butyl acetate; aromatic hydrocarbons such as benzene, xylene and toluene; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methyl ethyl ketone; aliphatic hydrocarbons such as hexane, heptane and octane; and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene; either alone or in combination of two or more thereof, but toluene, tetrahydrofuran or the like is preferably used.

The compound represented by Formula (1-3) may be obtained by reacting a compound represented by the following Formula (II-3b) with a compound represented by ArCH2X [the definition of Ar, A, Y and R3 has the same meaning as the definition described above, and X represents a halogen atom or OTs, OMs and the like] in the presence or absence of a base.

[Chemical Formula 21]

The compound represented by Formula (II-3b) may be synthesized by acting a sulfurizing reagent on a compound [the definition of A, Y and R3 has the same meaning as the definition described above] represented by Formula (II — 3c) , which may be synthesized in the same manner as described in Formula (II—1), in the presence or absence of a base. [Chemical Formula 22]

As the sulfurizing reagent, phosphorus pentasulfide, Lawesson's reagent, hydrogen sulfide and the like may be used. The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide; nitriles such as acetonitrile; sulfoxides such as dimethyl sulfoxide; ethers such as diethyl ether and tetrahydrofuran; esters such as ethyl acetate and butyl acetate; aromatic hydrocarbons such as benzene, xylene and toluene; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methyl ethyl ketone; aliphatic hydrocarbons such as hexane, heptane and octane; and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene; either alone or in combination of two or more thereof, but toluene, tetrahydrofuran and the like are preferably used.

The reaction may be performed usually at -80°C to 100°C, and is performed preferably in a range from 20°C to 80°C. [Chemical Formula 23]

The compound represented by Formula (1-4) may be obtained by reacting a compound represented by the following Formula (II-4a), which may be synthesized in the same manner as described in Formula (1-3) with a compound represented by R4-NH2 [the definition of Ar, A, Y, R4 and R5 has the same meaning as the definition described above]. [Chemical Formula 24]

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide; nitriles such as acetonitrile; sulfoxides such as dimethyl sulfoxide; ethers such as diethyl ether and tetrahydrofuran; esters such as ethyl acetate and butyl acetate; aromatic hydrocarbons such as benzene, xylene and toluene; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methyl ethyl ketone; aliphatic hydrocarbons such as hexane, heptane and octane; and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene; either alone or in combination of two or more thereof, but alcohols such as methanol and ethanol are preferably used.

The reaction, if performed in the presence of silver carbonate, copper carbonate and the like, progresses quickly, but may proceed without the compound.

The compound represented by Formula (1-4) may be obtained by reacting a compound represented by the following Formula (I-4b) or a salt thereof with R4-X, R4-0-R4 and R4-OR' [the definition of R4, R' , Ar, A, Y and R5 has the same meaning as the definition described above, and X represents a halogen atom] in the presence or absence of a base .

[Chemical Formula 25]

The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide; nitriles such as acetonitrile; sulfoxides such as dimethyl sulfoxide; ethers such as diethyl ether and tetrahydrofuran; esters such as ethyl acetate and butyl acetate; aromatic hydrocarbons such as benzene, xylene and toluene; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methyl ethyl ketone; aliphatic hydrocarbons such as hexane, heptane and octane; halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene; and water; either alone or in combination of two or more thereof, but toluene, dimethylformamide, acetonitrile, ethers, dichloromethane, chloroform and the like are preferably used.

The compound represented by Formula (I-4b) may be obtained by reacting a compound represented by Formula (Ilia) with ammonia or an alcohol solution thereof, ammonium chloride and the like.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide; nitriles such as acetonitrile; sulfoxides such as dimethyl sulfoxide; ethers such as diethyl ether and tetrahydrofuran; esters such as ethyl acetate and butyl acetate; aromatic hydrocarbons such as benzene, xylene and toluene; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methyl ethyl ketone; aliphatic hydrocarbons such as hexane, heptane and octane; halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene; and water; either alone or in combination of two or more thereof, but alcohols such as methanol and ethanol are preferably used.

The reaction may be performed usually at -80°C to 100°C, and is performed preferably in a range from 20°C to 50°C. [Chemical Formula 26]

The compound represented by Formula (1-5) may be obtained by reacting a compound represented by the following Formula (II-5b) with R6-X [the definition of AR, A, Y, R6 and R7 has the same meaning as the definition described above, and X represents a halogen atom], R6-0-R6 or R.6-0R' [the definition of R' has the same meaning as the definition described above] in the presence or absence of a base .

[Chemical Formula 27]

The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide; nitriles such as acetonitrile; sulfoxides such as dimethyl sulfoxide; ethers such as diethyl ether and tetrahydrofuran; esters such as ethyl acetate and butyl acetate; aromatic hydrocarbons such as benzene, xylene and toluene; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methyl ethyl ketone; aliphatic hydrocarbons such as hexane, heptane and octane; halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene; and water; either alone or in combination of two or more thereof, but toluene, N,N-dimethylformamide, acetonitrile, ethers, dichloromethane and chloroform are preferably used.

When R6 represents -C(=0)R6a [R6a has the same meaning as described above], the compound represented by Formula (1-5) may be obtained by reacting the compound represented by Formula (II — 5b) with a carboxylic acid represented by Rga_C (=0) OH [the definition of Rga has the same meaning as the definition described above] using a dehydration condensation agent in the presence or absence of a base, or may be obtained by performing the reaction using phosphorus pentaoxide, sulfuric acid, polyphosphoric acid, thionyl chloride, phosphorus oxychloride and oxalyl dichloride in the absence of a base.

It is possible to use a carbodiimide-based compound such as dicyclohexylcarbodiimide, l-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and the like as the dehydration condensation agent.

The reaction is preferably performed by using a solvent, and it is possible to use, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide; nitriles such as acetonitrile; sulfoxides such as dimethyl sulfoxide; ethers such as diethyl ether and tetrahydrofuran; esters such as ethyl acetate and butyl acetate; aromatic hydrocarbons such as benzene, xylene and toluene; ketones such as acetone and methyl ethyl ketone; aliphatic hydrocarbons such as hexane, heptane and octane; and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene; either alone or in combination of two or more thereof, but dichloromethane, chloroform and the like are preferably used.

When R6 represents -CONR6eR6f [the definition of Rge and Rgf has the same meaning as the definition described above, and R6e or R6f represents a hydrogen atom] or -CSNR6gR6h [the definition of R6g and R6h has the same meaning as the definition described above, and R6g or R6h represents a hydrogen atom], the compound of Formula (1-5) may be obtained by reacting the Formula (II-5b) with a compound represented by R''N=C=0 [R'' represents a Cl to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a (Cl to C4) alkoxy (Cl to C5) alkyl group, a (Cl to C4) alkylthio (Cl to C5) alkyl group, a substituted or unsubstituted (C6 to CIO) aryl group, and a substituted or unsubstituted 5- to 10-membered heterocycle] in the presence or absence of a base.

The reaction is preferably performed by using a solvent, and it is possible to use, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide; nitriles such as acetonitrile; sulfoxides such as dimethyl sulfoxide; ethers such as diethyl ether and tetrahydrofuran; esters such as ethyl acetate and butyl acetate; aromatic hydrocarbons such as benzene, xylene and toluene; ketones such as acetone and methyl ethyl ketone; aliphatic hydrocarbons such as hexane; heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene; either alone or in combination of two or more thereof, but nitriles such as acetonitrile are preferably used.

When R6 represents -CONR6eR6f [the definition of R6e and R6f has the same meaning as the definition described above], the compound of Formula (1-5) may be obtained by reacting the above-described compound represented by Formula (II-5b) with a compound represented by the following Formula (II— 5c) in the presence or absence of a base.

[Chemical Formula 28]

The reaction is preferably performed by using a solvent, and it is possible to use, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide; nitriles such as acetonitrile; sulfoxides such as dimethyl sulfoxide; ethers such as diethyl ether and tetrahydrofuran; esters such as ethyl acetate and butyl acetate; aromatic hydrocarbons such as benzene, xylene and toluene; ketones such as acetone and methyl ethyl ketone; aliphatic hydrocarbons such as hexane, heptane and octane; and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene; either alone or in combination of two or more thereof, but nitriles such as acetonitrile are preferably used.

The compound represented by Formula (II-5b) may be obtained by reacting the compound [the definition of Ar, A, Y and R.7 has the same meaning as the definition described above] represented by Formula (II-5a), which may be synthesized in the same manner as described in Formula (I-3) with hydroxylamine or a salt thereof in the presence or absence of a base.

[Chemical Formula 29]

The compound represented by Formula (1-5) may also be obtained by reacting the compound represented by Formula (II-5a) with a compound represented by R6-ONH2 or a salt thereof in the presence or absence of a base.

[Chemical Formula 30]

(1-6)

The compound represented by Formula (1-6) [the definition of Ar, A, Y, Ylf Y2,and Ry has the same meaning as the definition described above] may be obtained by reacting according to Phosphorus, sulfur, and silicon and the related elements (2006) 181, 2337-2344.

[Chemical Formula 31]

(1-7)

The compound represented by Formula (1-7) [the definition of Ar, A, Y, Ry and n has the same meaning as the definition described above] may be obtained by reacting a compound represented by the following Formula (II-7a) with a compound represented by ArCH2X [the definition of Ar has the same meaning as the definition described above, and X represents a halogen atom or OTs, OMs and the like] in the presence or absence of a base.

[Chemical Formula 32]

(II-7a)

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride and the like; a carbonate such as potassium carbonate or sodium carbonate and the like; an alkali metal hydroxide such as potassium hydroxide, sodium hydroxide and the like; tertiary amines such as triethylamine, 1,8-diazabicyclo[4.3.0]non-5-ene and the like; and unsubstituted or substituent-containing pyridines, such as pyridine, 4-dimethylaminopyridine and the like; as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when the solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide; nitriles such as acetonitrile; sulfoxides such as dimethyl sulfoxide; ethers such as diethyl ether and tetrahydrofuran; esters such as ethyl acetate and butyl acetate; aromatic hydrocarbons such as benzene, xylene and toluene; alcohols such as methanol, ethanol, propanol and isopropyl alcohol; ketones such as acetone and methyl ethyl ketone; aliphatic hydrocarbons such as hexane, heptane and octane; and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene; either alone or in combination of two or more thereof, but N,N-dimethylformamide and the like are preferably used.

The reaction may be performed usually at from 0°C to 200°C, and it is preferred that reagents are added at from 20°C to 40°C and the reaction is performed at from 60°C to 80°C.

The compound represented by Formula (II-7a) may be obtained by reacting a compound represented by (II-7b) [X represents a halogen atom, and the definition of Rz and n has the same meaning as the definition described above] with a compound represented by in the following Formula (III) in the presence or absence of a base.

[Chemical Formula 33]

(II-7b)

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when the solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile; sulfoxides such as dimethyl sulfoxide; ethers such as diethyl ether and tetrahydrofuran; esters such as ethyl acetate and butyl acetate; aromatic hydrocarbons such as benzene, xylene and toluene; alcohols such as methanol, ethanol, propanol and isopropyl alcohol; ketones such as acetone and methyl ethyl ketone; aliphatic hydrocarbons such as hexane, heptane and octane; and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene; either alone or in combination of two or more thereof, but N,N-dimethylformamide and the like are preferably used.

The reaction may be performed usually at from 0°C to 200°C, and it is preferred that reagents are added at from 20°C to 40°C and the reaction is performed at from 60°C to 8 0°C .

The compound represented by Formula (1-7) may be obtained by reacting a compound represented by (II-7b) with a compound represented by in the above Formula (IV) in the presence or absence of a base.

The reaction may be performed usually at from 0°C to 200°C, and it is preferred that the reaction is performed at from 0°C to 80°C.

Examples of a substituent that may be substituted of "a phenyl group which may be substituted" and "a 5- to 6-membered heterocycle which may be substituted", which are represented by Ar, include a halogen atom, a Cl to C4 alkyl group which may be substituted with a halogen atom, a Cl to C4 alkyloxy group which may be substituted with a halogen atom, a hydroxyl group, a cyano group, a nitro group and the like, preferably a halogen atom, a trifluoromethyl group and a cyano group, and particularly preferably a halogen atom.

Specific examples of the "a phenyl group which may be substituted" represented by Ar of a nitrogen-containing heterocyclic derivative compound having a 2-imino group represented by Formula (I) include a phenyl group and a 3-cyano phenyl group. "A 5- to 6-membered heterocycle which may be substituted", represented by Ar of a nitrogen-containing heterocyclic derivative compound having a 2-imino group represented by Formula (I) represents an aromatic 5- to 6-membered heterocycle including one or two of a heteroatom such as an oxygen atom, a sulfur atom or a nitrogen atom, specific examples thereof include a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a thiazole ring, an oxazole ring and the like, and preferable aspects thereof include a 6-chloro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6-trifluoromethyl-3-pyridyl group, a 6-chloro-3-pyridazinyl group, a 5-chloro-2-pyrazinyl group, a 2-chloro-5-pyrimidinyl group, a 2-chloro-5-thiazolyl group, a 2-chloro-4-pyridyl group, and more preferably a 6-chloro-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group and a 2-chloro-5-pyrimidinyl group.

Specific examples of "a 4- to 10-membered heterocycloalkyl group" represented by Ar of a nitrogen-containing hetero ring derivative having a 2-imino group represented by Formula (I) include a 2-tetrahydrofuranyl group, a 3-tetrahydrofuranyl group and the like and preferably a 3-tetrahydrofuranyl group. "A 5- to 10-membered heterocycle having a unsaturated bond including one or more nitrogen atoms", which A of a nitrogen-containing heterocyclic derivative having a 2-imino group represented by Formula (I) represents, means that [Chemical Formula 34]

in Formula (I) represents any one ring represented by each of the following Formulae A-l to A-40. In each formula, the end of a double bond is the substitution position of a nitrogen atom.

[Chemical Formula 35]

The ring is preferably the ring of Formulae A-l, A-13, A-14, A-15, A-16, A-23, A-25, A-38 and A-39 and more preferably the ring of Formula A-l. "A Cl to C6 alkyl group which may be substituted with a halogen atom", which Y represents, is an alkyl group having 1 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of halogen atoms which may be substituted is the number of hydrogen atoms which the alkyl group has. When a branched or cyclic alkyl group is included, it is obvious that the number of carbons is 3 or more.

Specific examples of "a Cl to C6 alkyloxy group which may be substituted with a halogen atom" which Y represents include a methoxy group, an ethoxy group, a trifluoromethyloxy group and a difluoromethyloxy group. A preferred aspect of Y is a hydrogen atom, a halogen atom or a cyano group, preferably a hydrogen atom or a halogen atom and more preferably a hydrogen atom. A preferred aspect of R is a group represented by the Formula (a), (c) and (d) described above. in Formula (I), "a substituted Cl to C6 alkyl group" which Ri represents is an alkyl group having 1 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted substituents is the number of hydrogen atoms which the alkyl group has. Examples of the substituted substituent include a halogen atom, a hydroxyl group, a cyano group, a nitro group, a phenyl group (this phenyl group may be substituted with a Cl to C4 alkyl group which may be substituted with a halogen, a Cl to C4 alkyloxy group which may be substituted with a halogen, a hydroxyl group, or a halogen atom), a phenoxy group (this phenyl group may be substituted with a Cl to C4 alkyl group which may be substituted with a halogen, a Cl to C4 alkyloxy group which may be substituted with a halogen, a hydroxyl group, or a halogen atom), a benzyloxy group (the phenyl group in this benzyloxy group may be substituted with a Cl to C4 alkyl group which may be substituted with a halogen, a Cl to C4 alkyloxy group which may be substituted with a halogen, a hydroxyl group, or a halogen atom), and the like. Specific examples thereof include a 1,1,1-trifluoroethyl group, a trifluoromethyl group, a trichloromethyl group, a difluorochloromethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a chloromethyl group, a difluoroethyl group, a dichloroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a difluorocyclopropyl group, a 2-cyanoethyl group, a 2-nitroethyl group and the like. A 1,1,1-trifluoroethyl group, a trifluoromethyl group, a difluorochloromethyl group, a difluoromethyl group and a pentafluoroethyl group are preferred, a trifluoromethyl group, a difluorochloromethyl group, a difluoromethyl group and a pentafluoroethyl group are more preferred, and a trifluoromethyl group are particularly preferred.

In Formula (I), "a Cl to C6 alkyl group which may be substituted with a halogen atom" which R3, R5, R7, Ry, and Rz represent is an alkyl group having 1 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted halogen atoms is the number of hydrogen atoms which the alkyl group has. When a branched or cyclic alkyl group is included, it is obvious that the number of carbons is 3 or more.

Specific examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a trifluoromethyl group, a trichloromethyl group, a difluorochloromethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a chloromethyl group, a difluoroethyl group, a dichloroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a difluorocyclopropyl group, a trifiuoroisopropyl group, and a hexafluoroisopropyl group, and the like. R3 is each preferably an ethyl group, an isopropyl group, a cyclopropyl group, a trifluoromethyl group, a difluorochloromethyl group, a difluoromethyl group and a pentafluoroethyl group, more preferably a trifluoromethyl group, a difluorochloromethyl group, a difluoromethyl group and a pentafluoroethyl group, and particularly preferably a trifluoromethyl group. R5 is preferably a trifluoromethyl group, a trichloromethyl group, a dichloromethyl group, a difluoromethyl group, a difluorochloromethyl group, a chloromethyl group and a pentafluoroethyl group, more preferably a trifluoromethyl group, a difluoromethyl group, a difluorochloromethyl group and a pentafluoroethyl group, and particularly preferably a trifluoromethyl group. R7 is preferably a trifluoromethyl group, a trichloromethyl group, a dichloromethyl group, a difluoromethyl group, a difluorochloromethyl group, a chloromethyl group and a pentafluoroethyl group, more preferably a trifluoromethyl group, a difluoromethyl group, a difluorochloromethyl group and a pentafluoroethyl group, and particularly preferably a trifluoromethyl group. Ry is preferably a methyl group, ethyl group, propyl group or isopropyl group. Rz is preferably a methyl group or trifluoromethyl group. "A Cl to C6 alkyl group which may be substituted with a halogen atom", which R2 represents, is an alkyl group having 1 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted halogen atoms is the number of hydrogen atoms which the alkyl group has. When a branched or cyclic alkyl group is included, it is obvious that the number of carbons is 3 or more. Specific examples thereof include a trifluoromethyl group, a trichloromethyl group, a difluorochloromethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a chloromethyl group, a difluoroethyl group, a dichloroethyl group, a 2.2.2- trifluoroethyl group, a pentafluoroethyl group, a difluorocyclopropyl group, a 1-(trifluoromethyl)ethyl group, a 1-trifluoromethyl-2,2,2-trifluoroethyl group, a pentafluoroethyl group, and a difluorocyclopropyl group, and the like, and preferred examples thereof include a 2.2.2- trifluoroethyl group, a 1-(trifluoromethyl)ethyl group and a 1-trifluoromethyl-2,2,2-trifluoroethyl group. "A Cl to C6 alkyl group which may be substituted" which R4 and R6 represent is an alkyl group having 1 to 18 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituents which may be substituted is the number of hydrogen atoms which the alkyl group has. When a branched or cyclic alkyl group is included, it is obvious that the number of carbons is 3 or more.

Examples of the substituent which may be substituted include a halogen atom, a hydroxyl group, a cyano group, a nitro group and the like. Specific examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an s-butyl group, a t-butyl group, a 3-methyl-2-butyl group, a 3-pentyl group, a 4-heptyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, an n-octyl group, an n-tridecyl group, an n-hexadecyl group, an n-octadecyl group, a trifluoromethyl group, a trichloromethyl group, a difluorochloromethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a chloromethyl group, a difluoroethyl group, a dichloroethyl group, a 2.2.2- trifluoroethyl group, a pentafluoroethyl group, a difluorocyclopropyl group, a 2-hydroxyethyl group, a 2-hydroxy-n-propyl group, a 3-hydroxy-n-propyl group, a 2,3-dihydroxy-n-propyl group, a cyanomethyl group, a 2-cyanoethyl group, a 2-nitroethyl group and the like. R4 is each preferably a methyl group, an ethyl group, a 2.2.2- trifluoroethyl group, a 2,2-difluoroethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, a t-butyl group, a cyclopentyl group, a cyclohexyl group and a 2-hydroxyethyl group, and more preferably a methyl group, an ethyl group and a cyclopropyl group. R.6 is preferably a methyl group, an ethyl group, an isopropyl group a cyclopropyl group, a t-butyl group and a cyanomethyl group, and more preferably a methyl group, an ethyl group, a cyclopropyl group and a t-butyl group. "A Cl to C6 alkyl group which may be substituted with a halogen atom", which R4a, R4b, R4c, R4d, R4e, R4f, R6a/ R-6bf R.6c, R6d, R-6ef R-6f/ ^6g, R-6hf R6i, R6j and R6k represent, is an alkyl group having 1 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted halogen atoms is the number of hydrogen atoms which the alkyl group has. When a branched or cyclic alkyl group is included, it is obvious that the number of carbons is 3 or more. Specific examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a trifluoromethyl group, a trichloromethyl group, a difluorochloromethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a chloromethyl group, a difluoroethyl group, a 2-chloroethyl group, a dichloroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a difluorocyclopropyl group and the like. R.6a is preferably a methyl group, an ethyl group, an isopropyl group and a cyclopropyl group. R.6b is preferably a methyl group. "A C2 to C6 alkenyl group which may be substituted with a halogen atom", which Ri, R2, R3, R4, R4a, R4b/ R4C/ R-4d/ R4e, R4f, R5 r R-6/ R6b/ R6df R6ej R-6f 1 R-6g / R-6h/ R-6i / R-6j / R6k 1 R7, Ry and Rz represent, is an alkenyl group having 2 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted halogen atoms is the number of hydrogen atoms which the alkenyl group has. When a branched or cyclic alkenyl group is included, it is obvious that the number of carbons is 3 or more. Specific examples thereof include an ethenyl group, a 1-propenyl group, a 2-propenyl group, a 2-fluoro-l-propenyl group, a 2-methyl-l-propenyl group and the like, and preferred examples thereof include an ethenyl group. "A C2 to C6 alkynyl group which may be substituted with a halogen atom", which Ri, R2/ R3, R4, R4a, R4b, R4c, R4d, R4e, R4f, R5/ Re / Rea/ R6b / R6c / R6d, R6e/ R6f / R6g / R6h, R6i / R6j / R6k/ R7, Ry and Rz represent, is an alkynyl group having 2 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted halogen atoms is the number of hydrogen atoms which the alkynyl group has. When a branched or cyclic alkynyl group is included, it is obvious that the number of carbons is 3 or more. Specific examples thereof include a 1- propynyl group, a 2-propynyl group, a 1-butynyl group, a 2- butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3- pentynyl group and the like, and preferred examples thereof include a 1-propynyl group, a 2-propynyl group and a 2-butynyl group.

The (C6 to CIO) aryl of "a substituted or unsubstituted (C6 to CIO) aryl group, a substituted or unsubstituted (C6 to CIO) aryl (Cl to C6) alkyl group, a substituted or unsubstituted (C6 to CIO) aryl (C2 to C6) alkenyl group and a substituted or unsubstituted (C6 to CIO) aryl (C2 to C6) alkynyl group", which R3, R4, R4a, R4b, R4c, R5, Re, Rea, Reb, Rec, R7, Ry and Rz represent, specifically represents a phenyl group and a naphthyl group, and the (Cl to C6) alkyl group, the (C2 to C6) alkenyl group and the (C2 to C6) alkynyl group may have a straight chain, branch or ring. Examples of the substituent which may be substituted with an aryl group include a halogen atom, a Cl to C4 alkyl group which may be substituted with halogen, a Cl to C4 alkyloxy group which may be substituted with halogen, a C3 to C6 cyclic alkyl group, a methylsulfonyl group, a methoxy group, a nitro group, a cyano group and the like. Specific examples thereof include a phenyl group, a benzyl group, a 2-phenylethyl group, a 2-phenylethenyl group, a 2-phenylethynyl group, a 4-methylphenyl group, a 2-cyanophenyl group, a 3-chlorophenyl group, a 4-methoxyphenyl group, a 3-cyanophenyl group, 1, 1-diphenylmethyl group, a naphthylethyl group, a naphthylpropyl group and the like, and preferred examples thereof include a benzyl group and a 2-phenylethyl group, a naphthylethyl group, a naphthylpropyl group.

The (Cl to C6) alkyl group, (C2 to C6) alkenyl group and (C2 to C6) alkenyl group of "a substituted or unsubstituted phenoxy (Cl to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group and a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group , Which R3, E-4^ R4a/ R4bf R4cf R5/ Re^ R.6af R-6b f R-6c f R7 / Ry and Rz represent, may have a straight chain, branch or ring. Examples of the substituent which may be substituted with a phenoxy group include a halogen atom, a Cl to C4 alkyl group which may be substituted with halogen, a Cl to C4 alkyloxy group which may be substituted with halogen, a C3 to C6 cyclic alkyl group, a methylsulfonyl group, a methoxy group, a nitro group, a cyano group and the like. Specific examples thereof include a phenoxy group, a phenoxymethyl group, a 2-phenoxyethyl group, a 2-phenoxyethenyl group, a 2-phenoxyethynyl group, a 4-chlorophenoxy group, a 2-methylphenoxy group and the like, and preferred examples thereof include a 2-phenoxyethyl group.

The 5- to 10-membered heterocycle of "a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (Cl to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group and a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group", which R3, R4, R4a, R4b, R4c, R5/ R6/ Rga, R6b, Rgc, R7, Ry and Rz represent, represents a ring including a hetero atom, such as an oxygen atom, a sulfur atom or a nitrogen atom as an atom constituting 1 to 4 rings, and examples thereof include a furanyl group, a thienyl group, a pyridyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a pyrimidinyl group, a morpholinyl group, a thiazolyl group, an imidazolyl group, a triazolyl group, a tetrahydrofuranyl group, a quinolinyl group and the like. Examples of the substituent which may be substituted with a heterocycle include a halogen atom, a

Cl to C4 alkyl group which may be substituted with halogen, a Cl to C4 alkyloxy group which may be substituted with halogen, a C3 to C6 cyclic alkyl group, a methylsulfonyl group, a methoxy group, a nitro group, a cyano group and the like. The (Cl to C6) alkyl group, (C2 to C6) alkenyl group and (C2 to C6) alkenyl group may have a straight chain, branch or ring. Specific examples thereof include a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 2-pyridylmethyl group, a 3-pyridylmethyl group, a 4-pyridylmethyl group, a 2-(4-pyridyl)ethenyl group, a 2-(4-pyridyl)ethynyl group, a 2-furanylmethyl group, a 2-thienylmethyl group, a 2-tetrahydrofuranylmethyl group and the like, and preferred examples thereof include a 2-pyridylmethyl group, a 3-pyridylmethyl group, a 4-pyridylmethyl group, a 2-furanylmethyl group, a 2-thienylmethyl group and a 2-tetrahydrofuranylmethyl group.

The (Cl to C4) alkoxy of "a (Cl to C4) alkoxy (Cl to C5) alkyl group, a (Cl to C4) alkoxy (C2 to C5) alkenyl group and a (Cl to C4) alkoxy (C2 to C5) alkynyl group", which R3, R4, R4af R-4b t R-4cf R6b/ R6c/ R6ef R6f r R7 and Rz represent, represents a (Cl to C4) alkyloxy, alkenyloxy and alkynyloxy having a straight chain, branch or ring. Specific examples thereof include a methoxymethyl group, a 2-methoxyethyl group, an ethoxymethyl group, a 2-ethoxyethyl group, a 3-methoxy-2-propenyl group, a 3-methoxy-2-propynyl group and the like. R4 is preferably a 2-methoxyethyl group.

The (Cl to C4) alkylthio of "a (Cl to C4) alkylthio (Cl to C5) alkyl group, a (Cl to C4) alkylthio (C2 to C5) alkenyl group and a (Cl to C4) alkylthio (C2 to C5) alkynyl group", which R3, R4, R4a, R4b, R4c, R5, R6, Rea, R6b, Rec, Ree, Rgf, R7 and Rz represent, represents a (Cl to C4) alkylthio, alkenylthio and alkynylthio having a straight chain, branch or ring. Examples thereof include a methylthiomethyl group, a 2-methylthioethyl group, an ethylthiomethyl group, a 2-ethylthioethyl group, a 3-methylthio-2-propenyl group, a 3-methylthio-2-propynyl group and the like. R4 is preferably a 2-methylthioethyl group.

The (C6 to CIO) aryl of "a substituted or unsubstituted (C6 to CIO) aryl group", which R2, R4cn R4e, R4f, Red, R6e, R6f, Reg, R6h, Rei, Rej and Rek represent, specifically represents a phenyl group and a naphthyl group, and the (Cl to C6) alkyl group, (C2 to C6) alkenyl group and (C2 to C6) alkenyl group may have a straight chain, branch or ring. Examples of the substituent which may be substituted with an aryl group include a halogen atom, a Cl to C4 alkyl group which may be substituted with halogen, a Cl to C4 alkyloxy group which may be substituted with halogen, a C3 to C6 cyclic alkyl group, a methylsulfonyl group, a methoxy group, a nitro group, a cyano group and the like. Specific examples thereof include a phenyl group, a 2-methylphenyl group, a 3-methoxyphenyl group, a 4- nitrophenyl group, a 4-cyanophenyl group and the like.

The 5- to 10-membered heterocycle of "a substituted or unsubstituted 5- to 10-membered heterocycle", which R2, R4d, FUe, R4f, R^dr R6e/· R6f/ R6g and R6h represent, represents a ring including a hetero atom, such as an oxygen atom, a sulfur atom or a nitrogen atom as an atom constituting 1 to 4 rings, and examples thereof include a furanyl group, a thienyl group, a pyridyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a pyrimidinyl group, a morpholinyl group, a thiazolyl group, an imidazolyl group, a triazolyl group, a tetrahydrofuranyl group, a quinolinyl group and the like. Examples of the substituent which may be substituted with a heterocycle include a halogen atom, a Cl to C4 alkyl group which may be substituted with halogen, a Cl to C4 alkyloxy group which may be substituted with halogen, a C3 to C6 cyclic alkyl group, a methylsulfonyl group, a methoxy group, a nitro group, a cyano group and the like. Specific examples thereof include a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 2-furanyl group, a 2-thienyl group, a 2-tetrahydrofuranyl group and the like.

As a preferred aspect of a compound represented by Formula (I), R represents the following Formula (a), [Chemical Formula 36],

Ar represents a 6-chloro-3-pyridyl group, a 2-chloro- 5- thiazolyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6- fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group, a 2-chloro-5-pyrimidinyl group, a 6-trifluoromethyl-3-pyridyl group and a 2-chloro-5-pyrimidinyl group, A represents a ring represented by A-l, A-13, A-14, A-15, A-l6, A-23 and A-38, Y represents a hydrogen atom and a 3-cyano group, and Ri represents a trifluoromethyl group, a difluoromethyl group, a chlorodifluoromethyl group, a pentafluoroethyl group, a trifluoroethyl group, an ethenyl group and a 2-propynyl group.

As another preferred aspect of a compound represented by Formula (I), R represents the following Formula (c), [Chemical Formula 37]

Ar represents a 6-chloro-3-pyridyl group, a 2-chloro- 5- thiazolyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6- fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group, a 2- chloro-5-pyrimidyl group and a 6-trifluoromethyl-3-pyridyl group, A represents a ring represented by A-l, Y represents a hydrogen atom, and R3 represents a trifluoromethyl group, a difluoromethyl group, a chlorodifluoromethyl group and a pentafluoroethyl group .

As still another preferred aspect of a compound represented by Formula (I), R represents the following Formula (d), [Chemical Formula 38]

Ar represents a 6-chloro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group and a 2-chloro-5-pyrimidyl group, A represents a ring represented by A-l, Y represents a hydrogen atom, R4 represents a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, a cyclobutyl group, a cyclohexyl group, and cyclopentyl group, and R5 represents a trifluoromethyl group, a difluoromethyl group, a chlorodifluoromethyl group and a pentafluoroethyl group .

As yet another preferred aspect of a compound represented by Formula (I), R represents the following Formula (e) group [Chemical Formula 39]

Ar represents a 6-chloro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group and a 2-chloro-5-pyrimidyl group, A represents a ring represented by A-l, Y represents a hydrogen atom, and

Rg represents a hydrogen atom, a methyl group, an ethyl group, a 2-propenyl group, a methylcarbonyl group, an ethylcarbonyl group, a cyclopropylcarbonyl group, an ethenylcarbonyl group, a 2-propynylcarbonyl group, a benzoyl group, a 3-pyridylcarbonyl group, a methyloxycarbonyl group and a phenyloxycarbonyl group, and R7 represents a trifluoromethyl group, a difluoromethyl group, a chlorodifluoromethyl group and a pentafluoroethyl group .

Specific examples of the compound of Formula (I) include a compound represented by a combination of the following Table A and Table B.

[Table 1]

[Table 2]

[Table 3]

Examples of more preferred compounds include N-[1-((6-chloropyridin-3-yl) methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound P212) and N-[1-((6-chloropyridin-3-yl) methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide (Compound 1-20), N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trif luoro-N'-isopropylacetimidamide (Compound 1-45).

In addition, in the present invention, an acid addition salt of a iminopyridine derivative represented by Formula (I) (preferably, an agriculturally and zootechnically acceptable acid addition salt) may also be used, and examples thereof include an acid addition salt such as hydrochloride, nitrate, sulfate, phosphate, or acetate and the like.

In the present invention, examples of honeybees (Apis) include Bombus, Meliponini, Apis dorsata, Apis dorsata laboriosa, Apis florea, Apis andreniformis, Apis mellifera, Apis cerana, Apis koschevnikovi, and the like. Among them, preferable are Apis mellifera and Apis cerana. Moreover, in the present invention, when mentioned, honeybees include all members in a population of worker bees, drones, eggs, larvae, pupas, and queen bees.

Examples of honeybee parasitic pests include honeybee microsporidia (Nosema apis), Varroa destructor, Acarapis woodi, honeybee Tropilaelaps,

Aethina tumida, Achroia innotata, Galleria mellonella (wax moth) , and the like. Among them, preferable are Varroa destructor, honeybee Tropi1ae1aps, and Acarapis woodi.

Examples of a plant serving as a honey source of honeybees include Fagaceae (Castanea, Castanopsis), Magnoliaceae (Liriodendroidae) , Theaceae (Camellia japonica, Eurya japonica, Camellia sinensis), Saxifragaceae (Deutzia crenata), Rosaceae (Prunus salicina, Prunus mume, Prunus persica, Prunus serrulata, Prunus avium, Eriobotrya japonica, Malus pumila, Pyrus pyrifolia, Fragaria χ ananassa), Fabaceae (Wisteria floribunda, Styphnolobium japonicum, Robinia pseudoacacia, Lespedeza, Trifolium, Astragalus sinicus, Vigna), Euphorbiaceae (Mallotus japonicus), Rutaceae (Zanthoxylum ailanthoides, Phellodendron amurensis, Fortunella, Citrus) , Anacardiaceae (Toxicodendron vernicifluum, Rhus javanica, Toxicodendron succedaneum), Hippocastanaceae {Aesculus), Aquifο1iaceae {Ilex rotunda, Ilex integra, Ilex serrata), Rhamnaceae (Hovenia dulcis), Tiliaceae (Tilia japonica), Cornaceae (Swida controversa), Araliaceae (Aralia elata, Eleutherococcus sciadophylloides, Kalopanax septemlobus), Clethraceae {Clethra), Ebenaceae (Diospyros kaki), Styracaceae (Styrax japonica),

Oleaceae (Ligustrum japonicum, Ligustrum obtusifolium) , Caprifoliaceae (Abelia * grand!flora, Abelia), Araceae (Acorus calamus), Polygonaceae (Fallopia japonica, Fagopyrum esculentum), Brassicaceae (Brassica rapa, Brassica oleracea), Cucurbitaceae (Sicyos angulatus, Cucurbita, Citrullus lanatus, Cucumis melo), Onagraceae (Oenothera tetraptera) , Asteraceae (thistles, Bidens, Taraxacum, Solidago canadensis, Cosmos, Asteroideae), Crassulaceae (Phedimus aizoon), Vitaceae (Cayratia japonica), and the like. A honeybee parasitic pest control agent of the present invention may be used alone, or as a honeybee parasitic pest control composition mixed with another pest control agent, or a mixture with another pest control agent when used. Examples of such usable other pest control agents include pest control agents other than the compound represented by Formula (I) and acid addition salts thereof. The examples are an insecticide, a fungicide, a miticide, a herbicide, a plant growth regulator, a control agent for animal parasites, and the like. Specific examples of the other pest control agents include fluvalinate, flumethrin, amitraz, cymiazole, coumaphos, etoxazole, formic acid, sucrose acid esters, fenpyroxymate, acrinathrin, thymol, organic acids such as β-acid derived from hop, and the like.

The honeybee parasitic pest control agent and the honeybee parasitic pest control composition used in the present invention can be applied by spraying, dipping, coating, smoking, applying, drenching, granule applications, and the like. Specifically, the honeybee parasitic pest control agent and the honeybee parasitic pest control composition may be used as follows. An undiluted stock solution of honeybee parasitic pest control agent and the honeybee parasitic pest control composition or a solution thereof diluted with water or an appropriate solvent may be directly sprayed onto honeybees and/or a hive thereof such that an active ingredient in the solution is applied in an effective amount. Alternatively, a paper or tape material, such as a sheet, processed into an appropriate shape (examples of the material include plastic, polyvinyl chloride, polyvinylidene chloride, polyethylene, polypropylene, polyurethane, polyvinylpyrrolidone, polyester, nylon, paraffin, tree bark, tree piece, and the like) may be dipped into, coated with, or kneaded with the stock solution or the solution diluted with water or an appropriate solvent such that the active ingredient is applied in the effective amount; then, the paper or tape material may be attached inside the hive or around the hive to bring honeybees into contact with the paper or tape material.

Moreover, in order to control honeybee parasitic pests, the honeybee parasitic pest control agent and/or the honeybee parasitic pest control composition containing the active ingredient may also be used in a method by which the honeybee parasitic pest control agent and/or the honeybee parasitic pest control composition are mixed with water or a feed such that the active ingredient is applied in the effective amount; and the active ingredient penetrates honeybees via water absorption, intake, or the like. Further, the following method may also be used: a plant serving as the honey source of honeybees is subjected to a chemical treatment by foliar treatment, seed treatment, nursery tray treatment, soil treatment, trunk injection, or trunk coating, using the stock solution of the honeybee parasitic pest control agent and/or the honeybee parasitic pest control composition containing the active ingredient or the solution diluted with water or an appropriate solvent, such that the active ingredient is applied in the effective amount; honeybees visiting flowers of the plant treated with the chemical absorb the chemical (active ingredient); and the honeybees come into contact with an untreated honeybee group in a hive, so that the chemical (active ingredient) is impregnated into the hive.

According to Nouyaku Kagaku Yougo Jiten (Terminological Dictionary of Agrochemical Science) (published in 1994 by Japan Plant Protection Association), the foliar treatment is a chemical treatment on a leaf or the crown of a plant. The seed treatment is an application (treatment) of a chemical or the like on a seed, a seed tuber, a bulb, or the like. The seed treatment is referred to as a chemical application to seeds in general. The soil treatment is an application of a chemical on the soil surface, or an injection or mixing into soil. The soil treatment is referred to as a chemical application to soil in general. The trunk injection is an application method by which a chemical having penetrating and migrating property is injected into a trunk or a root to thereby control a pest on the tree, wither a thicket to death, or for other purposes. The trunk coating is coating of a trunk (bark) of a tree such as a fruit tree with a chemical, and is also referred to as a bark treatment, by which a trunk of a tree is coated with a chemical having penetrating and migrating property to thereby control a pest, a trunk is coated with an adhesive to thereby capture a pest to death, a trunk is coated with a repellent to thereby protect the bark and the like from feeding damage by harmful animals, or for other purposes.

In addition, a nursery tray refers to a tray such as a cell nursery tray for raising seedlings of a plant. The nursery tray treatment is an application or irrigation of a chemical to a cell tray during seedling before transplanted to a field.

An effective concentration or an effective amount of the active ingredient, that is, the compound represented by Formula (I) and/or acid addition salts thereof contained in the honeybee parasitic pest control agent of the present invention and the honeybee parasitic pest control composition of the present invention is 0.000001% to 0.1% in the case where the chemical is directly sprayed to honeybees or a hive thereof; 0.01% to 50% of the weight of a material such as a sheet in the case where the material is dipped into or is coated with the chemical; 0.000001% to 0.1% of water or a feed in the case where the active ingredient penetrates honeybees via water absorption, intake, or the like; and preferably 0.1 g to 10 kg, more preferably 1 g to 1 kg, per 10 ares of cultivated land in the case of the plant foliar treatment. In the case of the seed treatment, the effective amount is preferable 1 g to 10 kg, more preferably 10 g to 1 kg, per 10 kg of the seed. Moreover, in the case of the nursery tray treatment, the effective amount is preferably 0.01 g to 10 g, more preferably 0.1 g to 1 g, per nursery tray. In the case of the soil treatment, the effective amount is preferably 0.1 g to 10 kg, more preferably 1 g to 1 kg, per 10 ares of cultivated land. In the case of the trunk injection or the trunk coating, the effective amount is preferably 0.01 g to 1 kg, more preferably 0.1 g to 100 g, per tree.

The present invention can provide the honeybee parasitic pest control agent and the honeybee parasitic pest control composition usually as a preparation in any dosage form of emulsifiable concentrates, liquid formulations, suspensions, wettable powders, flowables, dust, granules, capsules, tablets, oils, sheet preparation, aerosols, fumigants, and the like, by mixing at least one of the compound represented by Formula (I) and acid addition salts thereof, or at least one of the compound represented by Formula (I) and acid addition salts thereof and at least one of other pest control agents, with a pharmaceutically acceptable carrier such as appropriate solid carrier, liquid carrier, gaseous carrier, surfactant, or dispersant. The method for preparing these forms is not particularly limited, and a form can be selected depending on the use, and formulated according to a technique usable in general pesticide preparation.

Examples of the pharmaceutically acceptable carrier of the present invention include carriers such as a solid carrier, a liquid carrier, and a gaseous carrier; surfactants; dispersants; adjuvants, and the like.

Examples of the solid carrier include talc, bentonite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate, and the like.

Examples of the liquid carrier include alcohols such as methanol, n-hexanol, and ethylene glycol; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; aliphatic hydrocarbons such as n-hexane, kerosene, and lamp oil; aromatic hydrocarbons such as toluene, xylene, and methyl naphthalene; ethers such as diethyl ether, dioxane, and tetrahydrofuran; esters such as ethyl acetate; nitriles such as acetonitrile and isobutyl nitrile; acid amides such as dimethylformamide and dimethylacetamide; vegetable oils such as soybean oil and cottonseed oil; dimethyl sulfoxide; water; and the like.

Further, examples of the gaseous carrier include LPG, air, nitrogen, carbonic acid gas, dimethyl ether, and the like.

As the surfactant or dispersant for emulsification, dispersion, spreading and the like, it is possible to use, for example, alkylsulfate esters, alkyl (aryl) sulfonates, po1yoxyalkylene alkyl (aryl) ethers, polyhydricalcohol esters, lignin sulfonates or the like.

In addition, as the adjuvant for improving the properties of the preparation, it is possible to use, for example, carboxymethylcellulose, gum arabic, polyethylene glycol, calcium stearate or the like.

The aforementioned carriers such as solid carriers, liquid carriers, gaseous carriers, surfactants, dispersants and adjuvant may be used either alone or in combination, if necessary.

The content of active ingredients in the preparation is not particularly limited, but is usually in the range of 1 to 75% by weight for the emulsifiable concentrate, 0.3 to 25% by weight for the dust, 1 to 90% by weight for the wettable powder, and 0.5 to 10% by weight for the granular formulation .

[Examples]

Preparation Example 1 [Wettable powder]

Compound P212 10% by weight

Clay 70% by weight

White carbon 2% by weight

Diatomaceous earth 13% by weight

Calcium ligninsulfonate 4% by weight

Sodium lauryl sulfate 1% by weight

The ingredients were homogeneously mixed and ground to obtain wettable powder.

Preparation Example 2 [Water dispersible granule] Compound P212 10% by weight

Clay 80% by weight

Dextrin 5% by weight

Alkyl maleate copolymer 4% by weight

Sodium lauryl sulfate 1% by weight

The ingredients were homogeneously ground and mixed, water was added thereto to knead the ingredients thoroughly and then the mixture was granulated and dried to obtain water dispersible granules.

Preparation Example 3 [Flowables]

Compound 1-20 5% by weight POE polystyrylphenyl ether sulfate 5% by weight

Propylene glycol 6% by weight

Bentonite 1% by weight 1% xanthan-gum aqueous solution 3% by weight PRONALEX-300 (TOHO Chemical Industry Co., Ltd.) 0.05% by weight ADDAC827 (KI Chemical Industry Co., Ltd.) 0.02% by weight

Water added to 100% by weight

All the ingredients except for the 1% xanthan-gum aqueous solution and a suitable amount of water were premixed together from the blending, and the mixture was then ground by a wet grinder. Thereafter, the 1% xanthan-gum aqueous solution and the remaining water were added thereto to obtain 100% by weight of flowables.

Preparation Example 4 [Emulsifiable concentrate] Compound P212 2% by weight N,N-dimethylformamide 20% by weight

Solvesso 150 (Exxon Mobil Corporation) 68% by weight Polyoxyethylene alkyl aryl ether 10% by weight

The ingredients were homogeneously mixed and dissolved to obtain an emulsifiable concentrate.

Preparation Example 5 [Dust]

Compound P212 0.5% by weight

Clay 61.5% by weight

Talc 37% by weight

Calcium stearate 1% by weight

The ingredients were homogeneously mixed to obtain dust.

Preparation Example 6 [DL Dust]

Compound P212 1% by weight DL clay 96.5% by weight

White carbon 2% by weight

Light liquid paraffin 0.5% by weight

The ingredients were homogeneously mixed to obtain dust.

Preparation Example 7 [Microgranule fine F]

Compound P212 1% by weight

Carrier 95% by weight

White carbon 2% by weight

Hisol SAS-296 2% by weight

The ingredients were homogeneously mixed to obtain Microgranule fine F.

Preparation Example 8 [Granules]

Compound 1-20 2% by weight

Bentonite 40% by weight

Talc 10% by weight

Clay 46% by weight

Calcium ligninsulfonate 2% by weight

The ingredients were homogeneously ground and mixed, water was added thereto to knead the ingredients thoroughly, and then the mixture was granulated and dried to obtain granules .

Preparation Example 9 [Microcapsules]

Compound 1-20 2% by weight

Urethane resin 25% by weight

Sodium salt of naphthalene sulfonic acid formalin condensate 5% by weight 1,2-Benzisothiazolin-3-one 0.2% by weight Water 67.8% by weight

Microcapsules were obtained by forming a urethane resin coating on the surface of particles of the compound of the present invention by an interfacial polymerization method.

Preparation Example 10 [Sheets]

Compound P212 10% by weight oil 10% by weight

Polyvinyl chloride 80% by weight

The compound of the present invention and oil were mixed to obtain a mixture, sheets were obtained by surface of the Polyvinyl chloride was immersed in the mixture. Preparation Example 11 [Sheets]

Compound P212 10% by weight

Phthalic ester 30% by weight oil 5% by weight

Polyvinyl chloride 55% by weight

The ingredients were mixed and formed into a sheet-shape to obtain sheets. <Examples of Biological Tests>

Test Example 1 Pest control test of Varroa destructor

After anesthesized with carbonic acid gas, adults of Api s mellifera infected with Varroa destructor were subjected to a chemical treatment by applying the abdomens with an acetone solution of the compound according to the present invention at predetermined concentrations using a micro applicator. After the treatment, Apis mellifera were transferred into a plastic case and left to stand in a thermostatic chamber under dark at 25°C. During the test period, 50% sucrose water absorbed to absorbent cotton was provided as a bait.

Forty eight hours after the chemical treatment, the number of Apis mellifera survived and the number of parasitic Varroa destructor were examined. The mortality of the honeybees and the preventive value against Varroa destructor were calculated by the following equations.

Mortality (%) = { ( (100 - survival rate in u n treated plot) - (100 - survival rate in chemical treated plot) ) / (100 - survival rate in u n treated plot)} x 100

Preventive value = {(parasitism rate in untreated plot - parasitism rate in chemical treated plot)/ (parasitism rate in untreated plot)} χ 100

As a result, when Apis mellifera infected with

Varroa destructor were treated with 10 μς of the compound according to the present invention, a high preventive value was shown against Varroa destructor, and no Apis mellifera were killed.

Commercially available fluvalinate even at a smaller application dose of 5 μρ than that of the compound according to the present invention showed a mortality as high as 64%. In other words, it was confirmed that the compound according to the present invention acts as a chemical having both high efficacy against honeybee parasitic pests and high safety to honeybees.

[Table 5]

Mortality of honeybees

[Table 6]

Preventive value against Varroa destructor

Test Example 2 Pest control test of Varroa destructor

After anesthesized with carbonic acid gas, adults of Api s mellifera collected from a hive were grouped in test cages such that there were 10 to 20 heads per cage. Thereafter, the Apis mellifera were subjected to a chemical treatment by dipping the abdomens into an acetone solution of the compound according to the present invention at predetermined concentrations. After the Apis mellifera air-dried, the recovery of the Api s mellifera from the anesthesia was confirmed. Then, the cages were lidded to leave the Apis mellifera to stand in a thermostatic chamber under dark at 25°C. Note that 50% sucrose water absorbed to absorbent cotton was provided as a bait during the test period.

The number of Apis mellifera survived at 72 hours after the chemical treatment as well as the numbers of Varroa destructor parasitizing the Apis mellifera before the chemical treatment and at 72 hours after the chemical treatment were examined. The mortality and the parasitism rate were calculated by the following equations. The test was conducted in duplicate.

Mortality (%) = { ( (100 - survival rate in u n treated plot) - (100 - survival rate in chemichal treated plot) )/(100 - survival rate in untreated plot)} x 100

Parasitism rate (%) = (number of heads of honeybees parasitized by Varroa destructor/ number of honeybees survived) * 100

As a result, it was confirmed that dipping Api s mellifera in 10 ppm of the compound according to the present invention sufficiently reduces the parasitism rate by Varroa destructor.

[Table 7]

Mortality of honeybees

[Table 8]

Parasitism rate by Varroa destructor

[Industrial Applicability]

The pest control agent and the composition of the present invention as well as the pest control method using these in a throughput of the active ingredient as high as 10 μg per head of an adult do not show toxicity to honeybees but show high pest control effects on honeybee parasitic mites. Therefore, the present invention can greatly contribute to honeybee parasitic pest control.

The reference in this specification to any prior publication (or information derived from it), or to any matter which is known, is not, and should not be taken as an acknowledgment or admission or any form of suggestion that that prior publication (or information derived from it) or known matter forms part of the common general knowledge in the field of endeavour to which this specification relates.

Throughout this specification and the claims which follow, unless the context requires otherwise, the word "comprise", and variations such as "comprises" and "comprising", will be understood to imply the inclusion of a stated integer or step or group of integers or steps but not the exclusion of any other integer or step or group of integers or steps.

Claims

THE CLAIMS DEFINING THE INVENTION ARE AS FOLLOWS: [Claim 1] Use of at least one amine derivative represented by the following Formula (la) or an acid addition salts thereof as an active ingredient

(la) [wherein, Ar represents a pyridyl group which may be substituted with a halogen atom, a hydroxyl group, a Cl to C6 alkyl group which may be substituted with a halogen atom, a Cl to C6 alkyloxy group which may be substituted with a halogen atom, a cyano group, or a nitro group; or a pyrimidyl group which may be substituted with a halogen atom, a Cl to C4 alkyl group which may be substituted with a halogen atom, an alkyloxy group which may be substituted with a halogen atom, a hydroxyl group, a cyano group, or a nitro group, Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a Cl to C6 alkyl group which may be substituted with a halogen atom, a Cl to C6 alkyloxy group which may be substituted with a halogen atom, a cyano group, or a nitro group, and Ri represents a Cl to C6 alkyl group which is substituted with halogen] to control honeybee parasitic pests without killing the honeybees . [Claim
2] Use according to claim 1, wherein Ar is any one of a 6-chloro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group, or a 2-chloro-5-pyrimidyl group. [Claim
3] Use according to claim 1 or claim 2, wherein the honeybee parasitic pests are any one of Varroa destructor, honeybee Tropilaelaps, and Acarapis woodi. [Claim
4] Use according to claim 1 or claim 2, comprising spraying the active ingredient diluted with water or without dilution to a hive of honeybees such that the active ingredient is applied in an effective amount. [Claim
5] Use according to claim 1 or claim 2, comprising bringing honeybees into contact with a paper or tape material having been dipped into or coated with the active ingredient such that the active ingredient is applied in an effective amount. [Claim
6] Use according to claim 1 or claim 2, comprising mixing the active ingredient with water or a feed such that the active ingredient is applied in an effective amount. [Claim
7] Use according to claim 1 or claim 2, comprising subjecting a plant to any one of foliar treatment, seed treatment, nursery tray treatment, soil treatment, trunk injection, and trunk coating, using the active ingredient diluted with water or without dilution, such that the active ingredient is applied in the effective amount to thereby control the honeybee parasitic pests. [Claim
8] A method for controlling honeybee parasitic pests without killing the honeybees comprising applying to the honeybees an effective amount of at least one amine derivative represented by the following Formula (la) or acid addition salts thereof as the active ingredient

(la) [wherein, Ar represents a pyridyl group which may be substituted with a halogen atom, a hydroxyl group, a Cl to C6 alkyl group which may be substituted with a halogen atom, a Cl to C6 alkyloxy group which may be substituted with a halogen atom, a cyano group, or a nitro group; or a pyrimidyl group which may be substituted with a halogen atom, a Cl to C4 alkyl group which may be substituted with a halogen atom, an alkyloxy group which may be substituted with a halogen atom, a hydroxyl group, a cyano group, or a nitro group, Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a Cl to C6 alkyl group which may be substituted with a halogen atom, a Cl to C6 alkyloxy group which may be substituted with a halogen atom, a cyano group, or a nitro group, and Ri represents a Cl to C6 alkyl group which is substituted with halogen] [Claim
9] A method according to claim 8, wherein Ar is any one of a 6-chloro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group, or a 2-chloro-5-pyrimidyl group. [Claim
10] A method according to claim 8 or claim 9, wherein the honeybee parasitic pests are any one of Varroa destructor, honeybee Tropilaelaps, and Acarapis woodi. [Claim
11] A method according to claim 8 or claim 9, comprising spraying the active ingredient diluted with water or without dilution to a hive of honeybees such that the active ingredient is applied in an effective amount. [Claim
12] A method according to claim 8 or claim 9, comprising bringing honeybees into contact with a paper or tape material having been dipped into or coated with the active ingredient such that the active ingredient is applied in an effective amount. [Claim
13] A method according to claim 8 or claim 9, comprising mixing the active ingredient with water or a feed such that the active ingredient is applied in an effective amount. [Claim
14] A method according to claim 8 or claim 9, comprising subjecting a plant to any one of foliar treatment, seed treatment, nursery tray treatment, soil treatment, trunk injection, and trunk coating, using the active ingredient diluted with water or without dilution, such that the active ingredient is applied in the effective amount to thereby control the honeybee parasitic pests.